


Love in Enclosed Spaces

by somewhereelse



Category: Arrow (TV 2012)
Genre: Alternate Universe, Crossover, F/M, Mild Language
Language: English
Status: Completed
Published: 2018-10-04
Updated: 2018-11-17
Packaged: 2019-07-25 03:54:32
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 18,042
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16189547
Author URL: https://archiveofourown.org/users/somewhereelse/pseuds/somewhereelse
Summary: Thea Queen and Roy Harper have the ingenious idea to rip off some romcoms and set up their bosses’ love lives. Maybe then they would have some time for their own love lives. Now if only the damn workaholics would cooperate and fall in love already.A Set It Up AU





	1. Chapter 1

Ignoring the security guard’s protests, Roy slides across the top of the gate, like he would the hood of a car, hoping the sensor picks up his security card in time. It does, and the glass retracts just before his legs swing through. He lands on his feet a little unsteadily but keeps his balance enough to stumble into a sprint towards the open elevator doors. He’s too out of breath to call out a plea, but thankfully, the doors stay open long enough for him to slip through.

By a minor miracle, he manages not to spill the liquid gold—a very specific latte order from the place not across the street but two blocks down—on the other occupant or crush the fragile paper cup against the wall that stops his momentum.

“ _Fuck_ ,” he breathes in a sigh of relief as he bends forward to try to recapture his breath. When a throat clears, he straightens up a little self-consciously and sees a girl—woman? girl?—staring at him with clear amusement. “Sorry,” he pants, “Could you hit thirty-four?”

She obliges then goes back to watching him for entertainment. Eventually, she must take pity on him or feel some kind of kinship from being the only people crazy enough to be in this building this early, except for Security Dave who’s technically from the _night_ shift, because she reaches out to take the coffee cup so he can attempt to become human again, straightening out his clothes, picking his bag up from where he flung it into the elevator. He mumbles his thanks, and she acknowledges it with a nod.

“Crazy boss?” is the question that’s more of a statement.

“Yeah, a little,” Roy grins even though that’s not entirely true. Felicity’s demanding and particular and more than a little neurotic but never really unreasonable, per se. She just holds him to the same standard she holds herself. Too bad that standard is incredibly high and nearly impossible to reach. “You?”

She rolls her eyes at the understatement and hands him back the coffee. “I’m working for my brother. It’s going as well as that sounds.”

Roy pulls a face. He’s heard the horror stories about getting into business with family—or friends for that matter—and they almost make him glad to be an orphan. At least Felicity’s just an older sister _type_ and not his actual blood.

“Sorry, that sucks,” he laments. She sends him a sarcastic smile, and he realizes he should probably introduce himself to this girl if he’s going to keep chatting her up in this elevator. She’s hot, and providing a nice distraction from what’s sure to be a shitshow of a morning with the new product launch, and seems a little familiar. Maybe he’ll run into her again. “Roy. I’m an EA at Smoak Technologies.”

“A male EA?” she teases with a grin, “How progressive. Thea. I’m at QC.”

Roy notices then that she’s pressed the button for the fiftieth floor, AKA the executive suite for Queen Consolidated. “Thea _Queen_?” he fills in—no wonder she looked familiar—and she rolls her eyes, this time with annoyance. She thinks she knows where he’s going with that, but he hates being a known quantity. “I wouldn’t want to work for Oliver either. Heard his last three assistants quit or were fired within a month.”

Just as he expected, Thea looks grateful to be treated like any other assistant who’s trading some morning gossip. “That’s why I’m here. He can’t exactly fire me, and I can’t exactly quit. Mom really knew what she was doing when she had an heir and a spare.”

The joke catches him off-guard, and he’s trying to think of a good comeback, but the doors spring open. “Well, good luck to you, Thea Queen.” Raising the coffee cup in a mock salute, Roy walks backwards out of the elevator. He gives her a quick wink before spinning around just as the doors close.

“Roy! There you are!”

He jerks in surprise at the exclamation. Felicity’s leaning out of her office door, looking more than a little rumpled, and he silently groans, just knowing she spent the night here. He never should have trusted her when she said she’d leave an hour after he left last night. Without a word, he walks the coffee over to her, and she drains at least half of it before speaking again.

“Where have you been?”

“It’s 6:28,” he points out since their agreement is that he’s here by six thirty.

“Oh,” Felicity mutters then glances out her windows. The custom, adjustable tint has them mostly darkened, but the beginnings of the sunrise are creeping through. “I didn’t realize.”

He sighs, but she just shoots him a glare. “Don’t give me that look.” She disappears into her office so he turns and dumps his bag on his desk. A moment later, Felicity reappears with a sheepish smile. “But can you get me another one of those?”

With an indulgent sigh, he agrees, “Sure.”

 

* * *

 

The barista sends him a knowing look at seeing him back so soon. This time, he tacks on a coffee for himself before handing over his card. The drinks are ready in a few minutes—since it’s still asscrack of dawn early and there isn’t a line—and he backs his way out of the shop, the bell jingling behind him.

Across the street, he sees Thea Queen heading into the juice bar, the one Felicity refers to as green juice purgatory whenever she gets it in her head to go on a cleanse. She must see him, too, because she gives a friendly little wave that he returns with another cup salute since his hands are full.

Things might just be looking up.

 

* * *

 

Roy doesn’t even know how he got here.

That’s a lie.

He knows exactly how he got here. He picked the wrong pocket, or purse to be more accurate. Two hours later, the owner was banging on the door to his trailer. When he flung open the door in annoyance, he’d been napping to celebrate a successful day of hunting and gathering downtown, he didn’t expect to see an angry blonde girl—woman? girl?—on the other side.

“Seriously?” she practically yelled in his face. Then she looked past him into the trailer and repeated it again. “What is wrong with me? There’s being sympathetic, and then there’s being stupid. I mean, you’re the one who stole from me, and now I’m the one feeling sorry for _you_? God, I must be broken or something.”

“Excuse me?” he choked out because there wasn’t really a logical response to whatever she just said.

Barbie fixed him with a look. “Roy William Harper, Jr. Multiple arrests, charges, and convictions for robbery, larceny, grand theft auto, and _mayhem_? I didn’t even know that’s a crime. A couple assaults although those charges were dropped after witness testimony. Impressively, you’ve never served jail time, just community service. Which means either the Starling City public defender’s office is a lot more competent than anyone gives them credit for, or you’re good with your mouth.”

Immediately, his hackles rose, and he stepped forward to argue and maybe throw her off his porch. She beat him to it. “Oh my god! I did _not_ mean it like that. I wasn’t implying that you exchange, you know, for leniency. I just meant you’re probably good at talking your way out of trouble. Probably as good as I am at talking my way _into_ it.”

She’s so embarrassed that it drained away his anger and almost left him amused.

“I did not come here to make assumptions about you being a sex worker,” she sighed, rubbing at her forehead in irritation. “I came here to get my wallet back.”

Well, now he was definitely going to throw her off his porch.

“Hey, wait,” she held out a hand before he could, “Hear me out. I could have reported you to the cops but I didn’t. After looking into your background, I think I can help you as much as you can help me. You need a job, right? But you can’t get one with your record.” He reluctantly nods. “Well, I can offer you one. A legitimate, normal job with a steady paycheck that’s pretty decent.”

“What’s the catch?”

“Well, one, I want my wallet back. And, two, you’re going to anonymously send in whatever else you stole to the police so they can be reunited with their rightful owners.”

“And what’s the job?”

“I need an assistant.”

His kneejerk response is a “No.”

“Hey, _wait!_ God, you’re an impulsive one for someone with not a lot of options. Look, I need someone who can be a filter for all of this weirdness. I’ve got great ideas and more brains than I know what to do with but I can barely get anyone to take me seriously for obvious reasons. So I need someone who’s smart and resourceful and knows how to think on their feet, not these mousy, fawning idio— _people_ who keep yes man’ing me.”

“Still no.”

“Come _on_. The technology I’m developing could help save people’s lives. All I need is someone to con rich people into thinking, well, first, that you’re not a petty criminal, but, second, that I have enough _poise_ and shit to be a respectable businesswoman worthy of investments. Which, by the way, has nothing to do with the ability to actualize innovative biomedical technology. I just want to help people and bring some jobs back into this city.”

Roy wondered if she had some weird detector to find all of his soft spots. “I can’t believe I’m considering this. What about my record? You don’t care about that?”

“Nope,” she popped off with a triumphant grin. “I found you this time with five minutes and a cell phone. If you ever decide it’s a good idea to cross me, I’ll find you again and then I’ll technologically destroy you. I’ll ruin your financial prospects and put you on the terrorist watch list. Forget SCPD, I’ll have the FBI busting down your door. I might do it anyway if you don’t agree because, in case you haven’t noticed, I’m a little desperate for an unorthodox solution here.”

He scoffed in disbelief, but the smug grin on her face was too easy. Roy was born and bred with street smarts, and she’s not bluffing. Blondie’s capable of doing all that, and probably more, too.

“It’s pretty much an offer I can’t refuse,” he noted drily, and she nodded, holding out her hand. After a second of grumbling, he went back inside to retrieve her wallet.

He picked out the pink one, peeked at the license to see that her name’s Felicity Smoak, and returned to the door. She plucked it out of his hand and opened it to check the cards and cash in there. He hadn’t taken the time to empty them out so at least they won’t have to deal with that awkwardness.

“Great!” she enthused. “I sent details to your phone. Jeans are fine, but something nicer than a t-shirt would be great.”

Roy watched as she practically skipped back to her car. “See you tomorrow!” she called over her shoulder. Well, that was fucking weird.

But, yeah, he knows exactly how he got here.

 

* * *

 

Dave’s still pissy about his gate stunt this morning so there’s no one to talk to while he waits for the delivery guy to drop off his and Felicity’s dinner. Hell, Roy’s a little pissy because he had to promise the guy an extra twenty bucks to deliver this far away and this late. Because it’s like nine o’clock and reasonable people aren’t still in office buildings.

To echo his thoughts, he hears a voice behind him. “Hey, what are you still doing here?”

When he turns around, Thea is standing there, looking tired and barely holding onto her purse by her fingertips. In another life, he would have snatched and grabbed that thing fast enough to make her head spin. As a reformed citizen, he tries a charming grin instead. “Waiting for dinner.”

She shudders in response. “God, when do you _leave_?”

“Usually when Felicity does because if I leave, she’ll sleep here,” he admits with a shrug. Roy doesn’t even resent it anymore. She gave him a chance when no one else did, and is still, you know, keeping him off the streets, so the least he could do is look out for her a little.

“And I thought Ollie was bad. He only left “early” today—FYI, seven is not early—because he had this benefit to go to.”

“Then why are you still here?” Roy questions with interest. Growing up in Starling City, he would have never pegged spoiled princess Thea Queen to have a work ethic. Especially when their conversation this morning sounded like she’d been forced into the job.

“Needed to prep for the morning meetings,” she shrugs dismissively.

Apparently, he’s wrong about her. He’s never been more okay with that.

There’s a commotion at the front doors while Dave lets in the delivery guy. Roy turns to Thea with an apologetic smile before jogging away to exchange payment for food. The guy takes the extra twenty with a surprised look—apparently people lie about those types of things—and Dave stops pretending to harass him when Roy hands over an extra order of dumplings. Felicity was right all that time ago. He’s good at talking his way out of trouble and even better when he’s got a little cash to throw at the problem.

“Ooh, are those soup dumplings from May Wah?” Thea asks, leaning over to peek at the takeout boxes. He’s a little surprised to see her still there, but she’s probably just gathering energy to walk over to the parking garage. “Ollie took me there once after he got back from a few months in the Hong Kong office. Said they’re the most authentic ones in the city.”

“I have no idea about that, but they’re Felicity’s favorite. You want some? My dinner’s in here, too.”

Thea sends him a disbelieving look. “You’re working past nine, Roy. I’m not going to take part of your dinner, but thanks. I’ll see you around?”

“Count on it,” he agrees as she heads for the hallway to the garage.

 

* * *

 

“Is that yours or mine?” he asks around a mouthful of sandwich when a beeping interrupts their lunch.

After running into each other a few more times, they started eating lunch together whenever possible. The short time, sometimes literally only fifteen minutes before one of them has to go deal with one emergency or another, is quickly becoming his favorite part of the day.

Thea delicately pats her mouth clean with a napkin, but another beep interrupts her response. “ _Both_ ,” she answers with a dark look.

“Ugh,” she grumbles after glaring at her phone while he checks his to find a text from Felicity. “Ollie needs to get _laid_.” He has no idea what her brother sent to earn that reaction, but it makes him grin a little. “I’m guessing Felicity does, too.”

Roy just shrugs. It’s one thing for Thea to say those types of things—Oliver’s her brother—but Felicity is still his boss, even if they’re friends now. And it feels weirder, more inappropriate, because he’s a guy and she’s, you know, a _she_.

“We should totally set them up,” Thea mumbles as she taps out a response. “Felicity’s not Ollie’s “usual type”, but that could be a good thing. In any case, she’s still hot and successful. Ollie’s usually impressed by competent, intelligent women.”

Roy again shrugs noncommittally. Yeah, he’s got eyes. But she also does shit like figuratively sign his paycheck and literally give him an advance and obscure his criminal record so he can get a place  _not_ in the Glades. He tries not to think about Felicity’s relative attractiveness and is pretty good at it when no one’s making comments like that.

“What’s Felicity getting out of it?” Roy can’t help but ask after Thea finishes with the ways Oliver would be attracted to Felicity. So what if he’s a little protective of his mad scientist boss with a bleeding heart but zero social skills? Sue him.

“Good point. I hear Ollie’s not unfortunate looking—we do share the same genes after all—but I’m guessing Felicity’s not that shallow to only care about looks and money. Especially when they’re attached to a semi-reformed manwhore.”

“Wouldn’t know,” he answers after a few moments of consideration. That’s how long it took him to remember the last date she went on. Some forensic scientist who lives in Central City and he thinks they’re even still friends. As much as Felicity has friends outside of work. “Felicity doesn’t date enough to have a type, I’m pretty sure.”

“That’s unfortunate,” Thea frowns. “She’s hot and successful. What hope is there for everyone else?”

He notices Thea didn’t exactly lump herself in with the rest of the unwashed masses but ignores it. “Probably would help if she left her office in the daylight,” he suggests because, yeah, on paper, Felicity’s kind of a catch. “Or stopped refusing to download Tinder on principle.”

“Oh, no, I’m with her on that. Tinder is a trash place full of trash people. Dudes act like matching automatically entitles them to sex, and just _no_.” Thea shudders dramatically, and it’s not like Roy can knowledgeably disagree with the female perspective.

“What about you? Any romantic prospects?”

She’s looking at him speculatively. Roy can’t tell if she’s checking him out or trying to think of someone to set _him_ up with. He kind of hopes it’s the former. “Most days I’m the first one in this building and the last to leave. What do you think?”

“Fair,” Thea concedes with a laugh. “I’m not far behind you. If I knew how much this job would kill my social life, I would have put up more of a fight.”

Roy doesn’t know how to respond to that—it’s not like most other people have a _choice_ about working—so he starts to pack up his trash. Thea goes quiet and follows suit. She seems to know that what she said was a little snotty. To show there aren’t hard feelings, he takes her stuff and walks it over to the trash can.

When he gets to the door, she’s holding it open for him with a small grin. “I can’t complain too much, though. Wouldn’t have met _you_ otherwise.”

This time, her look is definitely flirty, and Roy returns it with a small smirk. They don’t really talk on the elevator ride, too busy exchanging sly glances. Normally, Roy wouldn’t hesitate to make a move but he kind of likes their pace, the whole being friends first thing. He thinks it’s different for Thea, too, given how much she gets chased after in the tabloids.

Just before they reach his floor, Thea pipes up. “You should think about it. Ollie and Felicity, I mean. I think they could be good together, or at least, you know, good for _us_.”

Roy makes a vague sound of agreement even though he knows he won’t. He’s got a good thing going here. His hourly pay is more than some college grads make, especially once overtime is factored in, and his ass barely got through high school. Then there’s his record to consider. No way he could get another job like this without someone like Felicity willing to overlook his past. And depending on how next quarter goes, Felicity wants to move him to a less time-consuming position so he can take night classes or something. And, yeah, that stuff she said back at his trailer about helping people and bringing jobs to the city? That’s pretty much exactly what they do.

He’s got a fucking chance and he’s not going to screw it up playing Cupid for his boss.

 

* * *

 

Then he finds Felicity sleeping in her office for the third morning in a row, and maybe Thea’s right about her needing a life, or at least a break.

 


	2. Chapter 2

Thea gets back to her desk to find Oliver pulling his hair out while ransacking her filing cabinets.

“Oh hell no! Back away!” she barks before he can do more damage. “I said I’d be up in ten minutes. You couldn’t wait?”

Without waiting for a response, Thea boxes him out of the space and pulls open the one drawer he hasn’t torn apart. She retrieves the file he’s been looking for and hands it to him with a pissy look. Oliver just glowers and, without so much as a “Thank you”, stomps back into his office.

Fucking ungrateful grouch.

If he keeps that up, she’s spitting in his afternoon coffee.

 

* * *

  

Thea always knew that, one day, her eavesdropping would land her in hot water.

“Oliver, this is the fifth one. You’re not convincing anyone that you’re bringing stability back to Queen Consolidated when you can’t even keep an assistant for longer than a month.”

_Ouch._

Fair, but still ouch. Thea knew Oliver had been trying lately to step into their father’s shoes, but trying didn’t mean succeeding. The papers were still waiting for him to fall flat on his face, and office gossip wasn’t doing him any favors.

“Well, _Mother_ ,” oh that tone was never a good sign, “I could do a lot more at QC if I had a competent assistant so I’m going to keep firing them until I find one that can keep up.”

“Another bad quarter, and you’ll be the one the board is tossing out,” Moira muttered dejectedly. She must have made some kind of noise, some indication that she was there, because Moira’s head whipped up and around. “Thea! Come in here please!”

Biting back the groan, she reluctantly shuffled into the living room. Moira was seated, back straight, ankles crossed, hands demurely folded in her lap, prim and polished as ever, but Oliver was pacing. His jacket was off, clothes otherwise rumpled, and hair messy. She got the feeling this wasn’t his first lecture today.

“I’ve had an excellent idea. You’re going to be Oliver’s assistant at work.”

“ _No!_ ”

The exclamation came from both of them. They exchanged a look, and Thea lifted a shoulder, letting him take the lead on this one.  
“Look, Mom. Thea and I, we love each other. So much, sometimes we want to kill each other. We can’t work together.”

“Yes, you can and you will.” Moira’s voice was resolute, like the time she read Oliver the riot act for having a pregnancy scare during college or last year when she drove drunk and wrecked her brand new car. “The survival of this company, not just your family legacy but the thousands of people Queen Consolidated employs, depends on our ability to weather this storm. I’m sorry if it is inconvenient and unideal for the two of you to work together, but so is the unemployment line. Every privilege you grew up with, you owe not just to me and your father but also to the hard-working people of this city who don’t deserve to lose their jobs in a hostile takeover because management couldn’t get their act together. So get your act together.”

Chastened, they chorused, “Yes, Mother.”

 

* * *

  

“How’s your self-destructing adult doing?” Roy asks, the next time they manage to have lunch together.

She gives a heavy sigh. “Worse. The Unidac auction is coming up so he’s stressing about that. Thinks Merlyn Global is going to swipe it out from under our nose.”

Roy nods. She’s mentioned it a time or two so she knows he’s got an idea of what she’s talking about. Plus, Smoak Technologies is on the periphery of the same industry so it’s probably in the universe of the news he reads. And, yes, he reads the news. More than she does, actually.

Roy’s told her only a little about his background. He doesn’t really seem embarrassed but, like, wary that she’ll hold it against him. It’s enough for her to recognize that they usually exist in entirely different worlds. He grew up rough in the Glades, ran into trouble with the law pretty often, and had little hope or opportunity for a better life until Felicity gave him a chance. So it makes total sense that he’s protective of her and willing to work the long hours she does. It’s also pretty likely that a background check wouldn’t clear him for another job somewhere else if he messes up at Smoak Tech.

Even if her family wouldn’t, Thea finds him impressive. She can’t imagine how she would have turned out without all the opportunities and second chances she’s had from being born into the right family. In fact, it’s kind of Roy’s example that’s got her sticking it out as Oliver’s EA. Otherwise, she would have walked out on his miserable ass within that first month like the others did.

“You know, I think Felicity might attend that.” The comment is casual, but she can read between the lines. “I’ve been trying to get her to socialize more and expand her network.”

Thea’s smile is immediate, and she lightly shoves his shoulder. “Bullshit,” she calls him out on the lame excuse. Smoak Tech was recently profiled by Forbes as an emerging company to watch. Felicity doesn’t need to go to the publicity when it’s coming to her. “You’ve been thinking about my suggestion.”

“Maybe,” he hedges with a slight grin. God, this guy’s jawline is fucking unfair. She wishes he’d make a move already, but the slow flirtation thing is kind of fun, exciting. “I think she slept in her office half of last week. I don’t care how comfortable her couch is, that’s just unhealthy. Maybe if she had a date or something, she’d actually leave.”

“You know, it wasn’t great when Ollie slept with anyone who had the right parts, but this isn’t much better. All he cares about is the company and making our parents proud, which is awesome and everything, but not exactly healthy. He needs a break, too. _I_ need a break,” she tacks on with a sigh.

Roy nods thoughtfully. “You think they’ve ever met before?”

“Maybe,” she shrugs because it’s within the realm of possibility. They both run well-respected companies in the same city and work in the same office building. “We need a meet-cute,” she snaps her fingers suddenly, “You know, like in the classic rom-coms?”

“You want to set it up so that she, like, spills a drink on him or something at the auction?” he asks skeptically. “I know we pretty much run their lives—tell them where to go and when and who to talk to and what to say—but I don’t think I can literally play Felicity like a puppet.”

“Okay, fine,” she concedes. Despite how much Oliver has come to rely on her for almost everything—she picks out his tie every morning for fuck’s sake—she can’t actually make him walk into another human being. He’s too coordinated for that. “We could at least make sure they meet there. QC’s always looking for a good JV partner.”

“So is Smoak Tech,” Roy adds. “Maybe that’s it. We can set up an investor meeting.”

“Mmm,” Thea hedges, “Actually, I don’t think we should mix business and pleasure. If it goes south, there’s no reason to let that affect the companies.”

If there’s anything she’s learned since being conscripted into employment as Oliver’s EA, it’s the extent of QC’s importance to the city. They employ so many people who depend on them for a livelihood, and she’s not going to mess around with that. Smoak Tech is also on the rise so Roy’s quick to agree.

They both fall silent, thinking it over. When she’s done with her salad, in what’s become a habit, Roy takes her container to the trash. Not until they’re standing in front of the elevator does the idea almost literally light up. Roy turns to her with a triumphant grin at the same time she snaps her fingers.

“The elevator!”

 

* * *

  

“Is now a bad time to mention that Felicity’s a little claustrophobic and a lot scared of heights?” Roy questions as he leans over the building engineer’s shoulder to peer at the security camera monitor.

Thea literally face-palms before shoving at his shoulder. “Yes, you goon, considering I just bribed Dig to shut down the elevator with them in it.” Her groan is only slightly exaggerated because if he shut it down, he can clearly start it back up with the push of a button.

“To be perfectly honest,” the engineer, John “call me Dig” Diggle, pipes up as the three of them lean closer to the small monitor to see if the occupants have moved beyond staring at their phones and ignoring each other, “I would have done this for free—I love love in enclosed spaces—but you did offer.”

“You could have said something before taking the money,” Thea grouses half-heartedly. It was a minor dent in her allowance/pay so it’s not like she’ll miss it, and she can’t exactly blame him for being opportunistic. Plus, she imagines this will be the best use of her spending cash in a _long_ while.

“Nice,” Roy commends the man before complaining, “Why don’t these things have sound?”

“That would be an invasion of privacy,” Dig explains distractedly.

They’re obviously talking to each other now that they’ve realized the elevator isn’t moving. Well, when Felicity isn’t frantically pressing buttons on the control panel.

Thea rolls her eyes, straightening up. “Which is exactly what I’m trying to accomplish here.”

Felicity must finally land on the emergency call button because a phone, buried under a pile of completed service requests, rings loudly, startling all of them. Dig answers on speaker, and Roy nudges her to stop her giggling.

“Maintenance,” Dig answers calmly, as if they didn’t concoct this exact scenario.

“Oh thank God! I’m in elevator four, and it’s stuck. At least I think it is because it’s not moving and the numbers aren’t lighting up. But I’m two seconds away from lighting up this jerk in here with me if that’ll improve your response time.”

She and Roy exchange a perplexed look at that last comment.

Felicity and Oliver haven’t met before this. They both confirmed it by casually dropping the other’s name, only to be met with distracted confusion. What could the dunce have said to her in the last minute to piss her off so badly?

“Ma’am, please remain calm. There’s definitely no need for violence,” Dig responds, a touch of actual alarm in his voice.

“Stop telling me to calm down! That’s what this jerk keeps saying.”

The look they share this time is knowing. Guess Felicity is _a lot_ more claustrophobic and scared of heights than Roy originally thought.

“Ma’am, the elevator isn’t stuck. You just happen to have boarded during the routine monthly maintenance. There should have been a sign on all call panels.”

That required a bit of work on their part. Dig printed them signs on the building stationery, and she and Roy placed them on every floor to discourage other stragglers from using the elevators at that approximate time. Then they had to remove the ones on floors where Felicity and Oliver, respectively, would board _before_ they boarded and then race down to the systems office using elevators Dig had waiting.

Dig steamrolls over Felicity’s huffy, “Well, there _wasn’t_.”

“Maintenance will be complete in fifteen minutes. Unfortunately, stopping the process will result in a thirty-minute restart before the systems come back online. But if you want me to, I could stop—”

“No! No! We’ll wait the fifteen. I promise not to kill him. Just don’t restart it!”

After Dig hangs up, they all exchange high fives. That was an impressive bit of lying and improvisation. For once, this might turn out to be a bribe that’s worth her money.

 

* * *

  

Roy’s got full-on grump face as he unwraps his sandwich.

“So that was a disaster,” she complains into her soup.

After ten more minutes of watching them look at only their phones and _not_ each other, they gave up and had Dig restart the elevator so they could get to the auction on time. And at the auction, despite her and Roy’s best efforts, Oliver and Felicity stayed on opposite sides of the room, engrossed in different conversations. Even though QC had the winning bid, Thea couldn’t help but be disappointed by the night.

“She’s getting worse. Which I didn’t think was possible,” he reveals with a concerned frown.

It’s one thing for their bosses to make their lives miserable, but it’s kind of compounded by the fact that she and Roy genuinely care about their well-being. Oliver’s actually her big brother, who, despite his asshole-ish tendencies, deserves some happiness in his life, and Felicity’s basically Roy’s big sister/guardian angel, who he wants to help in return. They can’t help but feel like failures.

“We need a new plan,” Thea decides impulsively. She’s not giving up on these idiots, no matter what Roy’s look of disbelief says.

“You know,” he begins skeptically, “we don’t even know if they’ll even _like_ each other. This is a lot of meddling to set up two people who don’t really have anything in common other than being workaholics.”

“Haven’t you heard the saying opposites attract?” Thea’s quick to point out. “I mean, it’s working for us, right?” she adds in the first open acknowledgment of the _thing_ they’ve got going on.

Roy’s smirk is somehow more _smug_ than usual. “Yeah, I think it’s working just fine. What’s your plan then?”

 

* * *

  

Thea signs Oliver up for a tech conference where Felicity is the keynote speaker. She justifies it to him as a good networking opportunity and a chance to actually learn something in the field where they just acquired Unidac. After a decent amount of bitching at her, he agrees to attend the keynote and the reception after.

She watches on the livestream link they received access to in exchange for low-level sponsorship. Despite Roy’s lackluster description of Felicity’s social skills—the reason she hired his pretty, charming, _conning_ face to act as her buffer against the outside world—Felicity’s a decently engaging public speaker. She’s obviously passionate and well-versed in her field and easily shuts down the people who have the gall to condescendingly question her expertise. The legitimate questions she actually fields.

Thea guesses Oliver would be impressed if at any point he looked up from his phone. She wants to send him a text that she can fucking see him in the front row reserved for sponsors, looking like an inattentive _ass_ , but that would reveal a level of interest in the conference that wouldn’t make sense.

Ugh. She’s got access to his email account. Those messages weren’t even _important_. It’s like he’s going out of his way to bungle the good thing she’s trying to do for him.

 

* * *

  

Roy convinces Felicity to attend one of the mixers QC puts on to defend its place atop the Starling City-based company food chain. It’s one of the few social events Thea doesn’t have to remind Oliver to attend since it gives him a chance to swing his dick around and assert QC’s dominance.

No matter how reformed he is from the publicly drunk mess he used to be, Oliver still hates losing.

Felicity spends most of the happy hour talking to Ray Palmer about their newly announced joint venture, and Oliver spends it trying to hide from Max Fuller’s ex-fiancée, who’s never gotten over being a pawn in a dick-measuring contest between two spoiled assholes.

Thea doesn’t even want Felicity seeing him in this state. If Oliver didn’t make a bad impression on her during their first two interactions, this would tank it for sure.

 

* * *

  

“This is getting fucking hopeless,” Roy complains one lunch.

He’s not wrong. It’s been months, and every set up they’ve tried has resulted in Oliver and Felicity either barely acknowledging each other or being completely oblivious. Thea would set her sights on a new target but with everything she’s learned about Felicity through Roy, she’s actually convinced they would make a good couple. Roy’s even grudgingly come around to the idea that they could actually be good for each other and more than just a temporary distraction.

This late in the game, it’s kind of too late to try to out-and-out set them up on a date. They run into each other at least ninety percent of the time Roy gets Felicity to leave her office. She and Roy can’t just throw them at each other on a blind date and hope it sticks. It has to be more _organic_ than that, aside from the part where it’s completely contrived.

“Tell me about it,” she grumbles in agreement.

Plus, they’ve been so preoccupied trying to make Oliver and Felicity happen, that she and Roy haven’t had a chance to happen. There’s a kind of unspoken agreement between them that they’ll make time for a date or _something_ once this plan comes to fruition.

“Okay, last-ditch effort,” Roy starts, turning slightly to face her. “The conference in Gotham.”

“Hmm, I’m a fan of the one-room, one-bed trope, but that’s a little aggressive.”

“ _What?!_ ” he seems genuinely concerned with where she took that. “Are you crazy? No. Hell no. I just meant get them sitting next to each other on the plane.”

Thea rolls her eyes to acknowledge the point. “Ollie usually takes the jet for events in Gotham so he can leave right after. He’s kind of a snobby prick like that.”

Roy sends her an amused look because that’s the exact type of thing he used to tease her for. At least they’ve moved past that.

“Can’t you say the jet’s out of commission or something? Or maybe get him to let Felicity to fly with him?”

She rolls her eyes so hard they might actually get stuck back there. “ _Please._ He’s such a diva. Ollie hates letting other people on the jet. We’ll have to think of something else.”

 

* * *

  

“Thea, do you have my hotel confirmed for Gotham?”

She glances up from her computer screen, worried that she’s starting to hallucinate. But, no, Oliver’s standing in front of her desk, waiting somewhat patiently.

“Uh, no,” Thea eyes him skeptically, “You never stay in Gotham. You always complain that it’s full of bats, psychotic criminals, and Bruce Wayne and that those things aren’t mutually exclusive.”

Despite the polished businessman act he’s been putting on, Oliver rolls his eyes at her. “Just get me a suite at the Grand,” he throws out before heading towards his office.

“Sure, no problem. I’ll just scrounge up a hotel suite on a conference weekend on forty-eight hours notice. That’s totally going to work, you out-of-touch idiot. Listen, I’m not going to get some poor receptionist fired because Oliver Queen is making unreasonable demands that couldn’t—and shouldn’t—be met. You can just come home after like usual.”

When he stops in his tracks to glare at her, Thea raises a challenging eyebrow right back. A few months ago, she wouldn’t have worried about raising hell to get what he—they—wanted, but she’s _grown_. Oliver’s whims aren’t worth this headache, for her or the unfortunate employee at the Gotham Grand. Thankfully, she’s in a position to put her foot down about it. It’s not like he can fire her for refusing.

“Fine, I suppose I can make another trip some other time,” he finally agrees with reluctance although Thea thinks she sees the hint of a smile. “But can you add Felicity Smoak to the flight manifest?”

It takes a second for her to shut her gaping mouth, but Oliver’s too preoccupied with his phone to notice her shock. “Felicity Smoak?” she repeats as if she’s unfamiliar with the name to try to hide her obvious interest. “Is that the woman who started Smoak Tech? You keep running into her, right?”

Oliver nods distractedly. “I ran into her in the elevator again just now. That new project Smoak Technologies has with Palmer Tech? We should have been on top of that. I offered her a ride on the jet to see what else she has in the pipeline.”

“Make her a captive audience, nice,” Thea says, pretending that all she cares about is the business angle. Oliver sends her a funny look at the unexpectedly drawn-out conversation so she distracts him with, “You know, I remember the good, ol’ days when you didn’t have to take a woman hostage to get her to talk to you.”

“Shut up, Thea,” he complains before really heading into his office.

Once his back is turned, she greedily grabs for her phone. Her hands shake with excitement as she types out a message to Roy.

TQ, 12:56 PM: OH. MY. FUCKING. GOD

 


	3. Chapter 3

Oliver Queen likes being the little spoon.

Felicity feels like that information ought to be worth something to Starling City society, although maybe it’s already a well-known fact. The point is, his cuddling preferences were unknown to her before this week. But no matter how they ended the night, if she woke up before him, it was with her face pressed to his muscular back.

Actually, maybe she just likes being the big spoon, and Starling City society’s appetite for that knowledge is definitely not the same. After all, there aren’t nearly as many articles about her as there are about Oliver Queen.

Yes, she checked.

Before they started this whole thing, she did her due diligence, writing a code to trawl the internet for Oliver’s most recent romantic encounters. The thing was, his encounters weren’t very recent at all. She doubted a man of his attractiveness and resources was entirely celibate, but it seemed Oliver had learned discretion since his debauched youth.

That was, an admittedly very small, part of why she considered this thing with him at all. The rest of her consideration had to do with his face and body and tendency to look at her like she was amazing and not some geeky weirdo. Oh, and the two weeks they spent eye-fucking. She never was great at the whole self-control thing.

Even though she probably—okay, very close to absolutely—would have still slept with him, the low probability of being documented as one of his many one night stands helped. In fact, Oliver didn’t treat her like a one night stand at all their first time, despite the conveniently located corporate apartment. He stayed the night for starters, although she guessed it would have been awkward leaving her at his company’s place. Since they’d been friendly acquaintances for a few weeks by then and he knew about her early mornings, he even woke her up with enough time for a quick shower and an even quicker wardrobe change at the office before Roy got there.

Ever since, Oliver has been attentive and considerate, aside from the whole pretending not to know each other in public thing. The entire thing so far has just been a lot more caring than his reputation lead her to believe. Felicity almost wants to pat herself on the back for not being so bowled over by his pretty face and Photoshop abs that she fell into bed with the personality of an overgrown frat douche.

“Solving world hunger back there?”

The question is mumbled and sleepy but still communicates his annoyance pretty well. Felicity comfortingly strokes his arm in a vague attempt to lull him back to sleep, but the strategy hasn’t worked yet. Once she’s up, he’s up. She doesn’t know how to answer, because it’s not like she wants to admit that she’s using all of her considerable brain power to figure out how to broach the relationship discussion and still coming up with zilch.

“If you’ve got the energy...” Oliver begins leadingly before, with what seems to require Herculean effort, flipping over to face her.

Felicity laughs, ignoring his frown. “You clearly don’t,” she points out obviously, and his frown turns into a pout. “It’s early still. Just go back to sleep.”

“You’re thinking too loud,” he grumps. “You know,” yawning shouldn’t be that attractive, “My R&D team would probably be pissed that we’re sleeping together.”

She raises her eyebrows in curiosity and offense. In his sleepy state, Oliver fails to pick up on the latter, just carries on with his random, half-awake thought. “Amazing orgasms are supposed to be mind-clearing. You know, release tension and get your creative juices flowing. From what I’m told, if we’re not careful, Smoak Tech is already going to start eating into our market share.”

Felicity laughs again, long and hard enough for Oliver to take offense this time. “You think, your sexual prowess is so mind-blowing—nay, universe-altering—that it’s going to unlock some secret compartment in my brain and give me ideas to decimate QC?”

“You don’t have to laugh that much,” he pouts, and she apologetically strokes a hand down his chest. “I was just saying that they should be mad at me, but it wouldn’t matter anyway. It’s been a week, and I still haven’t turned your brain off.”

Oh. My. God.

Is he really offended he hasn’t been able to tire her out enough that her overactive, constantly buzzing mind shuts down?

Fine, then.

“Maybe you just need to put your back into it,” Felicity challenges, and pretty soon, she has to take back her words about Oliver not having the energy.

 

* * *

 

Roy peers at her suspiciously when he comes in with her morning coffee.

The ends of her ponytail are still damp, and her makeup is so fresh she worries it hasn’t fully set yet. Self-consciously, Felicity smooths out her top before fixing him with her own skeptical look. “What?”

“Is that— Didn’t the dry cleaners drop that dress off yesterday?”

He sounds incredulous and worried, which is an interesting combination for a guy who tried to slam his door in her face the first time they met. Roy’s taken on the unlikely but somehow natural role of concerned brother. Every time, it makes her heart swell a little. At least until she remembers his line of questioning.

Before she can attempt to come up with an undoubtedly bad lie, he sighs irritably. “Damn it, Felicity. You need to go home and sleep. How many times do we have to have this discussion? If you don’t start taking care of yourself, I’m going to have to resort to drastic measures.”

Oh, okay. So he just thinks she’s been sleeping on her office couch again. Well, that’s better than the alternative, she supposes.  But still, the implied threat almost makes her smile. Like what he is even going to do?

“Drastic measures? What does that mean?” Her lips are pursed in an attempt to hide her laughter, but he can hear it anyway.

Roy glares at her teasing disbelief. Sometimes, she forgets what a rough upbringing he had and how creative and resourceful he had to be to survive on his own for so long. He runs a hand through his hair, the motion dripping with frustration.

“I don’t know. I honestly don’t know what else I can do to help you.”

The amusement drains out of her. Suddenly, all she can feel is the guilt of making Roy worry. He mumbles something under his breath before kicking the floor and leaving her office.

Well, that couldn’t have gone worse.

 

* * *

 

“Do you think we should tell them?”

His question comes, thankfully, after they have and once he’s no longer inside her. That might be blunt, but it’s not like her accidental innuendos have ever done her any favors.

“Tell them what?” Felicity asks breathlessly, challengingly. Maybe she hasn’t really tried to define this thing they’re doing—stress relief? the beginnings of a relationship? a monumentally bad decision that’s going to end in a broken heart for her?—but Oliver gets downright squirmy about it.

True to form, he dodges what she considers the obvious interpretation of her question. “You know, to stop trying to set us up.”

“Is that what they’re doing?” She’s being obtuse on purpose, and Oliver knows it based on the dark look he gives her. “I hadn’t noticed,” Felicity stubbornly persists.

To hell with it.

If this is how it ends, then this is how it ends. They’ve been benefiting with each other for nearly a month now, and she refuses to keep giving away the milk for free, even though that’s a lot like shutting the barn door after the horse. Mixed farm metaphors aside, what started as mutually beneficial stress relief is now stressing her out. So it’s time to figure out if this is a thing that’s going to keep her heart racing in a good way, or if she should go back to toying with how to improve actual pacemakers.

“It’s completely obvious,” Oliver straightens up in bed to frown down at her, “Thea and Roy have been trying to get us together for at least a month. You haven’t noticed?”

“Well, I guess you’re always at those events Roy sends me to, but so are Ray Palmer and Ted Kord. I figure it’s just a small business community in Starling City.” That was the same reasoning Roy gave her when she asked him last week if he had some sort of agenda in forcing her out of the nest. Man, her brain is really stuck on animal metaphors right now. “But if you think Roy and Thea are crazy enough to be playing matchmaker in their very limited spare time, then by all means, tell them to stop.”

“Roy’s your assistant,” Oliver points out, rather obviously. “I can’t exactly tell him what to do.”

“Well, I don’t think he’s doing anything other than scheduling more social events so what do you want me to say to him?” Felicity supposes she’s just going to commit to digging this hole.

“Tell him to stop conspiring with Thea.”

“Conspiring? You think your sister is conspiring against you? That’s a little dramatic. I think they’re just on the verge of dating, and making us go to the same events just gives them one more excuse to talk to each other.” There. That’s a good enough excuse that’s also entirely plausible given the barely suppressed flirty looks the pair keep exchanging.

“Felicity.” Based on his look, she’s taken the playing blonde act too far. “You know what they’re doing. Why don’t you want to talk to Roy about stopping?”

Of course, she knows what they’re doing. She’s not deaf. Roy sits right outside her office, and her door is open more often than not. She would have to be hard of hearing and completely oblivious to miss how frequently he talks to someone named Thea, the start of which happened to coincide with Thea Queen’s well-publicized employment at Queen Consolidated.

At first, she thought it was just Roy having a thing—a likely requited thing for how much they talked and were seen in each other’s company—for the notoriously unobtainable Queen heir, which good for her for having standards. Felicity applauded their connection because Roy’s past and relatively low position on the totem pole shouldn’t affect his love life. Despite his rocky start and in addition to his boy band good looks, Roy has a great heart, an impressive work ethic, and loyalty in spades. If Thea Queen can appreciate those qualities without judging his past, then she clearly isn’t as empty-headed as she’s painted to be.

But then their thing became furtive. Suddenly, Roy was encouraging her to get out more, like a lot more. He said it was because her social skills really had improved since he first started working for her and if he was going to transition out of being her assistant, then she needed to get used to a more normal, more traditionally credentialed assistant. In short, she had to become accustomed to being the name and the face of Smoak Technologies.

From there, a pattern quickly emerged. Roy cut off any conversation he was having with Thea whenever she appeared, which could have had to do with the unspoken personal calls policy. But he also signed her up for a lucky streak of events with one thing—one person—in common.

The jerk she nearly kneed in the nuts during that elevator fiasco.

While she’d been having a meltdown in an elevator, Oliver Queen had been all the worst qualities that she initially tried to write off as tabloid slander. He was selfish and condescending and self-involved and rude and just generally an asshole. That she considered his sobriety an actual positive quality spoke to how poor an impression he made.

Then he approached her after that keynote address. He was surprisingly apologetic about how he handled the elevator night, blamed it on being preoccupied with the Unidac auction, where she’d determinedly avoided him. Even more surprisingly, Oliver was interested in her talk, despite how she saw him in the very front row and consistently on his phone. Apparently, it was all just a little too over his head and would she mind explaining it more?

He invited her out for drinks which somehow turned into dinner. All throughout, Felicity felt like she was in some manufactured rom-com where the guy’s actually impressed by the smart girl and not put off by her foot-in-mouth syndrome. Oliver actively listened to her while also being self-deprecating and family-oriented and tentative yet cocky. By the end of the night, Felicity was the one reminding herself not to invite him into her bed.

The next week they ran into each other at after work events again. Twice. Which is approximately when she started suspecting Roy of foul play, although she kept that to herself for awhile.

Neither of them seemed to want the scrutiny that would come from two prominent public figures in the city dating so they had an unspoken agreement to keep it low-key, meeting up after events in quieter, lesser known places then pretty quickly moving on to each other’s places. She was both impressed with herself and worried with how easily she adapted to slipping Oliver subtle cues, or picking up on his, to confirm their meetings. Oliver, of course, seemed to have no issue with it, probably having all the experience with low-key hook-ups.

Except now Felicity’s worried it’s become  _too_  low-key.

She’s uninterested in running herself ragged to be Ollie Queen’s sidepiece. The last few weeks where Roy kept finding her asleep in her office in the middle of the afternoon was from trying to maintain her grueling workload while also making time for this  _whatever_  with Oliver. It’s unsustainable, and something is going to give soon. Unless Oliver’s willing to invest and acknowledge the relationship-ness of all this, Felicity’s not going to neglect her company for the sake of admittedly mind-blowing but casual sex.

Now to make Oliver understand all that without issuing an ultimatum, of sorts, that would prematurely scare off infamous playboy Ollie Queen. She doesn’t think he’s the same douchey frat boy from the papers, not by any stretch of imagination, but old habits die hard, and he’d probably bolt if she approaches the conversation wrong. Which is very likely. Despite all of Roy’s help to socialize her, word vomit is still her most comfortable communication method so Oliver’s just going to have to deal with it.

“Oliver, apparently my life is so pathetic, my assistant, who, granted, is also a friend slash younger brother, felt it necessary to meddle in a pretty drastic and ridiculous way. As if that’s not bad enough, you want me to tell him to stop, not because my life has gotten less pathetic but because  _why_?”

Oliver stares at her like she’s lost her mind. Apparently, the reasoning is obvious for him. “He’s crossing a whole bunch of lines and boundaries that are grounds for you to fire him?”

Right.  _That_. But, “Crossing lines and boundaries would be making an employee feel personally responsible for ensuring that I eat regularly and leave the office at night. I’ve taken advantage of Roy, like you’ve taken advantage of Thea. I know she’s your sister so it’s a little different, but we rely on them for pretty much everything. We expect them to make our lives run so smoothly, they thought we wouldn’t notice if they set up a relationship like they set up our meetings and appointments.”

She wants to be mad at Roy. She  _should_  be mad at Roy. But even if he’s doing this to create some benefit for himself—she suspects time off for a social life, specifically for a date with Thea Queen—he’s also doing it out of concern for her. It’s hard to separate the personal and the professional with them, especially given their unusual meeting and fast friendship. They’ve been in each other’s personal business pretty much since day one and never bothered to redraw the boundaries. At this point, Roy’s her family like Thea is Oliver’s.

“It’s a serious invasion of privacy, but that’s pretty much the entire point of their jobs, to invade our privacy. They know our personal information, our credit cards, our schedules, our food preferences, who knows what else. They could have made our lives miserable in retaliation for running them ragged all the time. Instead, they tried to make us happier. So what  _exactly_  do you want me to tell Roy to stop doing?”

Oliver blinks slowly. For a moment, she thinks he’s going to be  _real_  with her. The way he lets her see how heavily his family legacy and QC’s continued success weighs on his shoulders, or how he regrets the time and opportunities he wasted before his father’s death, or how much he  _tries,_  not just to uphold the company reputation or his lifestyle, but also for each and every employee at QC. In a split second, it’s gone, and he’s flashing her a salacious grin.

“I want you to tell him to stop trying to set you up, whether that’s Ray Palmer or Ted Kord or  _me_. Because you already have your hands full.”

Granted, Oliver says all this while doing his level best to leave a hickey somewhere that will hopefully be covered by the dress she brought over, so it’s not entirely her fault that she doesn’t notice how he completely, again, dodges defining this  _thing_.

When she finally does regain her wits and Oliver’s grinning at her with a smug but proud and adoring expression, Felicity can’t bring herself to call him out again, not if this is what she’ll lose. Maybe if she just gives him a little more time, things will work out.

Mentally, Felicity scoffs. She didn’t build up Smoak Tech to where it is on blind luck and wishes.  Perseverance and a willingness to confront challenges head-on is what’s lead to her hard-won success. She gets the feeling that’s what’s going to be required with Oliver, and until she confronts her overfull schedule and self-esteem issues and actually tries to have an honest conversation with him, she can’t actually pull the plug yet. 

 


	4. Chapter 4

_Fuck._

Felicity looks good sprawled out in his bed. Although, it’s not really his bed. It’s the company’s bed in an apartment they rent to house executives visiting from other offices. In fact, the last person to utilize this apartment before them was probably, shudder, his father and one of the assistants he slept with. That little bit of history makes him feel dirty, unseemly somehow, even though there is nothing as tawdry about his relationship— _thing_ —with Felicity.

To prove it, he leans down to try to wake her. He’s not sneaking out in the dead of the night like she’s some regrettable one night stand. No, it’s early morning because he consciously chose to spend the night with her, and they _both_ have to be at work in relatively short order.

He’s been trying to show her, through _action_ , that he’s _in_ this. That she’s different for him, and that, despite their unorthodox beginnings, they are not a momentary distraction. To be honest, Oliver’s not entirely sure it’s working.

“Hey,” she nuzzles against the hand he lays on her cheek, and his chest swells with emotion he’s not going to try to figure out right now, “Felicity, wake up. We’re going to be late.”

At the magic words, she practically jackknifes upright, and he rocks back on his heels to avoid getting whacked with a flailing limb. “I’m awake! I’m awake!”

Oliver nearly laughs at her overreaction before he sobers. Felicity’s so accustomed to brief snatches of sleep that anything more causes her to panic. Despite being half-dressed, he takes his chances and crawls back into bed with her, holding her tight to soothe her confusion.

“You know, I would have preferred this to the first attempt,” she grumbles against his chest. Oliver knows she doesn’t mean it since she’s also gone completely lax under his hands stroking down her naked back. “What time’s it anyway?”

“Five-thirty,” he mutters. As expected, the strategy is backfiring because he’s now relaxed himself and completely unwilling to leave this bed. “I just wanted you to have enough time to shower.”

“The office is across the street.” Her response is accusatory and disbelieving. “God, I hope Roy left my dry cleaning there. Going to have to change in the bathroom again.”

“Me too,” he sighs with annoyance. “I think Thea tags my shirts and ties like they’re an endangered species population she’s trying to track.”

“Oops.” They both smile at the memories of the many dress shirts he’s already had repaired due to her impatient hands. “Come on,” Felicity begins, rolling out from under him and onto her feet. She pads across the hardwoods to the bathroom and finishes with a casual “Join me,” over her shoulder.

Oliver has no idea what awkwardness everyone else is talking about. Felicity Smoak’s ability to close a deal is unparalleled.

 

* * *

 

They didn’t get off to the best start. Which was, admittedly, his own fault.

Sure, he noticed the beautiful woman who boarded the elevator after him, but it was kind of an important night, and he was no longer the guy who cornered beautiful women in their place of work. So he did his best to ignore her, checking for last-minute updates about the auction on his phone.

When the elevator jerked to a stop and she started panicking, he wasn’t the most sympathetic human being on the planet. In fact, Felicity would later tell him he’d been rude and abrasive and totally deserving of her threat to light his ass on fire. In his defense, he’d just gotten word that Ray Palmer was suddenly considering bidding on Unidac. Fucking billionaire genius who couldn’t be satisfied with his domination of Coast City.

Oliver figured that was the last he’d see of Elevator Girl. Who knows how many people worked on the fifty odd floors of the building? But then, Thea sent him to that tech conference, citing a need for him to be visibly interested and invested in their newest acquisition. He ended up in the front row, completely amazed and bowled over by the brilliant woman on stage.

How was he supposed to know Elevator Girl was otherwise known as Felicity Smoak, the rarely seen but highly praised founder and CEO of Smoak Tech?

To cover for his complete lack of knowledge on the topic, he focused on his phone, answering the emails and texts that trickled in during her keynote. After, he gathered his courage to approach her at the reception, apologizing for his behavior during the elevator incident and inviting her to a reconciliatory drink. After all, QC’s often in the market for a good JV partner, and Smoak Tech’s rapidly on the rise. He needed to mend fences before it was too late and he lost her—future opportunities to collaborate with her, that is—to someone like Ray Palmer.

Of course, drinks turned into dinner as he grew captivated by Felicity’s passion and dedication. She wasn’t just brilliant but irreverent and funny and almost completely without pretense, as long as he didn’t insult her intelligence. He could see how others might find her frustrating—accidental innuendos and endless tangents—but those things just added to her appeal in his opinion. Then there was how _little_ she was impressed by him, evaluating his tenure at QC through the lens of “But what have you done _lately?_ ”

Felicity didn’t hold his past, good _or_ bad, against him. She just wanted to know how he was trying to do and be better. It was a way of being held accountable that was unfamiliar yet thought-provoking for him.

By the end of the night, there was definitely the potential for her to invite him over. He’s received invitations on much less promise. But despite their chemistry, she bid him farewell with a professional handshake that lingered maybe a moment too long. Oliver watched her slide into a cab with a contemplative look and a tingling in his fingertips.

Felicity Smoak had just thrown down a gauntlet, whether she knew it or not, and Oliver Queen loved a challenge.

In the next week, he saw her again at another reception and then a fundraiser. Both times, they greeted each other briefly but didn’t spark like during their dinner. Oliver was all set to chalk it up as a fluke until the third event when he saw Felicity huddled in a corner, frowning into her wine glass.

That’s when he realized it.

They both wore masks at events like this. QC was recovering but still vulnerable, and Smoak Tech was under constant scrutiny as people waited for the young female CEO to misstep. Neither of them could play at flirting, or even just being friends, with all eyes on them.

So Oliver bucked up his courage again.

He approached her at the coat check and, very quietly and very discreetly, asked her to dinner at a small Italian place he knew just outside the Glades. Everyone knew the food at these events was lackluster and unfilling, so she agreed with a small smile. Sure enough, the moment they were seated in a dark corner, they fell back into that easy, comfortable conversation. With one difference. This time, even more than the last, every look and every word was loaded with intention.

Oliver wasn’t at all surprised when they fell into bed together after maybe two weeks of “friendly” dinners. Dinners neither of them, very specifically, ever called dates. He wouldn’t have minded waiting even longer for her, but Felicity’s impatience got the better of both of them, much to their mutual pleasure.

Now he’s at a loss for what to do.

Here’s this woman, the first he’s actually, really liked in a long time, and in one part of his life, he barely knows her. Pretends not to, at least. All the while, his little sister and Felicity’s assistant are cooking the books to make them run into each other at every possible opportunity. He’s starting to think even the elevator incident was rigged.

Oliver wants to tell them to stop, just because it’s annoying, but that might mean he’ll see Felicity less if Roy’s not constantly doctoring her schedule. And if he’s somehow wrong, if this is really just coincidence, Thea might get the idea that he doesn’t appreciate the work she’s been doing, and he doesn’t want to discourage her. Like their mom said, they needed to get their act together, and with someone he trusts running the front office, who has a vested interest in the company’s success and who he can’t just steamroll over, QC has been flourishing. Well, at least the board only brings up firing him every other week, instead of every week.

Most importantly, Felicity’s probably reaching the limit of her patience for him waffling around. Contrary to popular belief, he’s not actually stupid. Maybe unmotivated on occasion, but this isn’t one of those occasions. He can read Felicity in the way she tenses up after making any reference—accidental or purposeful—to the “what are they doing here” of it all and stays tense until he sexes it out of her.

Then there’s the way she’s always looking at him. Don’t get him wrong, he likes the attention and would normally revel in it. But this gaze is different than the pleasantly surprised, admiring one of their early days, at least once he won her over. Nowadays, Felicity stares at him like she’s performing a mental cost-benefit analysis. Oliver can’t figure out which side of the equation he’s landing on, and it makes him twitchy.

Saying this is new for him is an understatement.

They have actual conversations. Like he wants to talk to her. Not for corporate espionage but just to see if she and Curtis worked out the design flaw in their prototype because it’s all they thought about for seeming weeks except she was also trying to hammer out a new parental leave policy with her outside counsel. He’s only expected to handle one of those things, and she can apparently do both at the same time in _less_ time, and he just never wants her to stop talking, to stop being brilliant. It’s a sharp contrast to how he’s felt about most other women he’s been with, when all he’s wanted is for them to stop talking.

Her interest is waning, he can tell. He’s not nearly as smart or as interesting as her, and even though she still looks at him like like he’s more accomplished, a better human being, than he really is, Felicity’s getting bored or restless or something. He needs to up the ante and he knows what will move them along, but the words always die on the tip of his tongue.

He can do this. He can keep Felicity charmed and satisfied until he works out the words. It’s not even _those_ three words. A simple acknowledgement of the seriousness, the importance, of their relationship would be enough at this point, but he’s got some sort of impostor syndrome holding himself back. It’s like he’s waiting for Felicity to realize she can do better, even for a booty call.

But it does get easier with the more time they spend together. Each night, his heart nudges his mind a little further along the path of acceptance. He’s just waiting for the day when the two organs reconcile, but until then, he can fake it until he makes it. Just as long as _Felicity’s_ not the one faking it.

 

* * *

 

The feeling of panic is unexpected.

And weird.

He’s Oliver Queen. He doesn’t panic.

But there’s Felicity, zipping up her dress, a task he would normally be all over helping her with, and talking about her week-long trip to Gotham.

Of course, he knows that the conference is coming up, that Smoak Tech would be in attendance as they’re unveiling three new prototypes, that Felicity would obviously be there for her company’s success. Even if Thea didn’t schedule him to be there for the day of presentations, he would have found a way to be in the bat-infested city anyway. Oliver just didn’t realize she’d be gone a _week_.

Ever since they started their _thing_ , they’ve made time for each other at least every couple days. He hasn’t gone an entire week without seeing Felicity, never mind engaging in their extracurricular activities. And, no, that’s not the only part of her absence that concerns him.

Felicity in Gotham during the National Technology Conference is borrowing trouble. Oliver’s convinced that the only reason he’s held her interest this long is because she’s starved of better options in Starling. With how much of herself she gives to her work, it’s not like Felicity has all this extra time to devote to dating. Whenever she does leave her office to attend some networking event, he’s right there, always just _around_ to remind her how great he is at giving her orgasms.

But Gotham’s a different story. The conference will be a sausage fest of dicks who can actually follow her trains of thought. That realization is the source of his panic.

It wasn’t supposed to happen like this, but Felicity Smoak makes him nervous and insecure and prone to irrational jealousy because he still can’t do the thing where he acknowledges how important she is to him.

The question bursts out of him. “Why don’t you fly with me to Gotham?” Somehow, he doesn’t regret asking.

“You hate Gotham,” she retorts automatically, knowingly, skeptically.

If there were any doubts about how much he’s let her into his life, that right there would be wipe them away. All his mother’s training would never let him admit he didn’t like something to anyone. That type of information could be leveraged against him at a future date, so the strategy was to always pivot away from potential bad publicity. But Felicity knows his dislikes, and his likes, as well as he knows hers. So why can’t he just admit how much he likes her before she fully settles into the idea that they’re just a fling?

Oliver shrugs, hopefully casually. “Doesn’t get me out of this conference. Come on, it’s environmentally friendly. We can... discuss upcoming projects during the flight.”

With a frown, Felicity reminds him, “We agreed not to mix business.” Oliver breathes a chuckle, because of course she somehow missed that proposition, then raises an eyebrow. “ _Oh!_ You’re talking about _sex_. I want to but I can’t, Oliver. I need to focus on these presentations.”

“I’ll help you,” he offers a little too eagerly. Felicity raises her own eyebrow but suspiciously instead of suggestively. “Really. It’s not like I would, or even can, steal your ideas twelve hours before you launch prototypes, and I’m the perfect guinea pig since I don’t understand anything and you’ll have to dumb it down for me. Lowest common denominator and all.”

She smiles indulgently and steps closer to wrap her arms around his neck. “You’re _not_ dumb.” He scoffs in the face of her vehement insistence. “You’re not, Oliver. You need to stop selling yourself short. I wouldn’t be with someone who couldn’t hold his own.” Felicity turns away then to collect her shoes, and he’s momentarily distracted by the view.

Then they both freeze. She straightens hurriedly then pauses in the act of turning to face him. Oliver can practically picture her mouthing her countdown, even if all he can see of her is her back.

This is it. This is his chance. He slides a hand onto her lower back and presses a kiss below her ear. “Thank you,” he breathes, sincerity weighing down every syllable.

Felicity turns, eyes perusing his face carefully, before she smiles. Oliver cringes internally. He’s been stringing along this amazing woman for so long, that even his barely implied confirmation that they’re “with each other” can bring a beaming smile to her face. “Sometimes, I don’t know why you put up with me,” he adds in a mutter.

This time, Felicity’s grin is quick and flirty, taking a page out of his book for avoiding their heavy moments. “Because you have a private jet that I can’t wait to tour.” Her fingers start working at the knot in his tie at the same time his find the zipper to her dress.

They’re both late to the office.

 

* * *

 

His heart clenches and his stomach sinks with every step he takes onto the jet. Alone. No blonde genius to accompany him and marvel, with more than a little bit of censor in her tone, over the extravagant excess of a private jet.

No, he left Felicity half an hour ago, being fawned over by the usually misogynistic and difficult to impress tech industry. He just barely caught her eye before she was mobbed by the adorers, Curtis’ afro being the only marker of where her petite stature was in the crowd. Not a minute later, his phone beeped with a reminder to leave for the airport, and he reluctantly turned his back. Felicity wouldn’t be back for days yet, and he was leaving her in a veritable paradise.

The flight back to Starling feels long and too quiet, no matter how much he tries to distract himself with the emails that piled up while he was enraptured by Smoak Tech’s presentation. The next few days pass in a daze, enough that Thea asks what’s crawled up his ass and died. He waves her off unconvincingly and tries not to think about how he can’t even text or call or email Felicity with the unrestricted access Roy and Thea have to their respective accounts and phones.

Then one morning, he wakes up to the sensation of a bundle of warmth settling into his arms, soft hair tickling his chest and neck. “Felicity?” he mumbles hopefully around the scratchiness in his throat.

“Hi,” she returns brightly, far too brightly for how early it has to be. When he does squint an eye open, she’s smiling at him patiently even as she practically vibrates with excitement. “Morning!”

That chirp is an octave higher, and he breathes a chuckle, rolling over until she’s pinned beneath him. “ _Very_ good morning,” he returns, leaning down for a lengthy “God I missed you so much” kiss. Whatever has Felicity excited must really be exciting because she quickly breaks it off then pecks him again when a pout forms.

“The greatest thing happened yesterday, Oliver, and I couldn’t wait to tell you in person. I kind of pinged your phone, sorry,” she winces.

Only then does Oliver remember that he’s in the corporate apartment, because somehow it just felt easier sleeping there in the last place where he was with Felicity. She’s never officially had a key, but it’s an electronic lock so she’s pretty much always had a key. Oliver shrugs away her apology. He doesn’t care how she found him, just that she’s back.

“What’s going on?” he prods, leaning in again to rub his nose against hers.

Felicity reels back an inch, staring at him with both amusement and curiosity. Okay, fine, he’s not normally this affectionate with anyone really, but he’s _missed_ her. Before she can ask the obvious question, he slants his mouth over hers again for another deep, drugging kiss.

When they pull back, Felicity is distracted by his lips, her bright fingernails tracing along the bottom one. “Come on, what’s the good news?” he reminds her again, almost smiling when she visibly shakes herself back to the moment.

“Oh!” she lights up, “We doubled our funding for the microchip!”

The second she finishes the exclamation, Felicity kisses him hungrily, obviously in the mood to celebrate. Oliver’s so into helping Felicity out of her plane clothes, yoga pants and a light sweater, that his brain forgets to filter the personal comments he would usually hold back. Without his noticing, a stream of “You’re remarkable”s and “I’m so proud of you”s slip out while he’s reacquainting himself with her naked body. 

But, unlike for him, the uncharacteristic remarks break Felicity out of the sex-daze. “What?” she chokes out with disbelieving laughter.

Brain frozen, Oliver just smiles before leaning in to kiss her again. Felicity allows it for a few seconds then pulls back, one hand coming up to grip his jaw and squish his mouth. “No, no, no,” she mutters when he frowns, lips all contorted in her hold. “You can’t just drop statements like that and try to wipe it from my mind with your ridiculous kissing talents.”

“What?” he tries for nonchalance, “I think you’re incredible. You know that.”

“Yeah, but that’s, like,” Felicity waves her free hand, “in a general, vague way that, like, the mothers of little girls I’ve never met probably think I’m a good example. That’s, well, that’s a weird way of saying that. I don’t—” She closes her eyes and heaves a sigh.

With a curious frown, Oliver waits her out. He knows their arrangement has caused her some amount of stress, mainly in the form of how could she lower herself to continue sleeping with him. Up until right now, he hadn’t even considered that their undefined relationship might have an impact on her opinion of herself.

“Are you”—she peeks an eye open to squint at him, a wince twisting her features—”personally invested in this? In _me?_ ”

He nods slowly, “Of course, you’re my—”

Her other eye eases open, both eyebrows hitching up in hopeful question.

 _Now or never_. Oliver exhales a slow breath, a hesitant, nervous smile trying to form. “I mean, do you want to— I would like you to—”

With a breathy laugh, she cuts off his pathetic mumbling, “Why are we like this?”

The acknowledgment of both their roles in this unspoken mess breaks the heavy tension. As much as he’s been avoiding the conversation for his own insecurity-related reasons, Felicity’s also been extremely careful to avoid putting too much pressure on him, probably for the very visible reasons perpetuated by his media coverage. Their relationship discussion is long overdue, especially if it keeps him from being as miserable as he’s been the last few days, feeling as if he lost her without ever really having her.

“Commitment-phobia?” he ventures, grinning.

Felicity quirks a smile then lobs back, “Abandonment issues?”

“Workaholics?” they chorus before chuckling at themselves.

“We’re pathetic,” she mutters, “There are high schoolers who can DTR better than us. For frak’s sake, we’re adults. _Successful_ adults successfully adulting and making decisions that impact employees and bottom lines, and for _whatever_ reason, we can’t just—”

Her rambling makes him smile. Oliver can’t remember the last time someone other than Felicity made him smile. (Usually there’s Thea, but the roles of CEO and executive assistant have redrawn their lines in a strange way. He needs to work on that because the last thing he wants us to lose his little sister to the business.)

“I like you,” he states clearly and without hesitation, “I like you so much more than just a fling and incredible sex. You’re incredible and going to do so much good in the world—already _are_ doing so much good—and I can’t believe you want anything to do with me.”

Felicity looks startled by his easy admission. And it _was_ easy. So easy, Oliver has no idea why he’s been holding back those words for so damn long.

“I, uh, well—” For once, Felicity’s too flustered for words, and the amusement must show on his face because she smacks his bicep ineffectually. Her mouth opens and shuts a few times while a blush, probably from his praise, works its way down her neck. Oliver’s about to work his own way down her neck when she sheepishly offers, ”Samesies?”

It’s stupid how adorable he finds the simple, almost juvenile reciprocation, but he does. With his lips pressed together to stifle his laughter, Oliver sweeps down to kiss the still-red Felicity, but she slaps a hand over his mouth. His eyebrows twist up to express his displeasure at another interruption.

“No, wait, I can do so much better than that. I mean, not as good as you because you’re surprisingly eloquent when you want to be, and I mainly just ramble but I can do better than an expression popularized by _Superbad_. Because I’m an adult and I should express myself better than high schoolers, even if they are played by twenty-something’s in a movie with a script.”

Oliver quirks a slight smile at her because, yeah, the words would be nice but, “Our offices open in about an hour, and we could be having sex right now.”

“Like we need that long,” she retorts with a hand wave, “Yeah, yeah, be smug about it.” He _absolutely_ will. Quantity _and_ quality when it comes to their orgasms. “Give me a minute. I didn’t exactly plan on having this conversation anytime soon.”

Her lips purse, and her forehead wrinkles. Oliver contents himself with watching her microexpressions and subtly trying to slide a hand under her ass until she swats away his wandering hand. Finally, her expression lights up, and she grins at him.

“You’re ridiculous.”

“Excuse me?” he asks, eyebrows jumping in offense.

“Yeah,” Felicity nods enthusiastically, “You’re absolutely ridiculous. It’s ridiculous how much and deeply you care, not just about the money but about this city and doing right by the people who’ve worked hard to build up QC. And it’s ridiculous how you try so hard to put up this façade of nonchalance when you’re just so dedicated to the people you love. And it’s ridiculous that this is the package you come in. And it’s ridiculous that you wanted to yell at Roy and Thea for trying to set us up when it’s probably their best idea ever. And it’s ridiculous that just seeing you is the highlight of my day, although _abs_ so that tracks a little bit. And it’s ridiculous that you can’t believe I want anything to do with you when it’s me who should think that about you. Did that make sense?”

Oliver pretends to think about it even as he fights back his own blush. “Passionate, well-supported by multiple examples, parallelism. _Perfect_ ,” he declares, “just like you.”

With an eye roll, Felicity repeats her mantra, “You’re ridiculous.” He’s about to kiss the smug grin off her face, but she stops him for the third time. “Fifty minutes, don’t you have a point to prove?”

Gauntlet thrown, he doesn’t give her another chance to interrupt.

 

* * *

 

“Are we going to tell them?” Felicity asks, her lips pursing in a contemplative frown.

Oliver snorts. “Hell no. They can figure it out themselves.”

Grinning, Felicity leans up to peck his lips in an achingly familiar gesture that he’s missed these last lonely mornings. Her hand lingers on his tie, disturbing it so she can take the time to straighten it, and it’s his turn to lean down for another kiss. Then he happily watches her sashay across the street towards her coffee shop before he turns the other way to the office.

 


	5. Chapter 5

John Diggle is invisible.

Or so he kids himself. Long ago, he grew used to being unseen by the ever busy office drones of the building best known for housing the headquarters of Queen Consolidated. After the first few times they saw him, once they got over his sheer size, often clothed in a mid-market suit but occasionally coveralls, he disappeared into the monotonous background of their office environment.

That is, until one day, when he was accosted by the living embodiment of sunshine.

 

* * *

 

“Excuse me, but I think I can help?”

He looked up from where he’s elbow deep in the guts of an elevator control panel to find a blonde woman, glasses and all bright colors, peering around the propped open doors and the short out of order sign. Confounded, he blinked at her a few times before returning his attention to the problem at hand. “Thanks, but somehow, I think this is outside your wheelhouse.”

“You don’t know my wheelhouse,” was the prompt response. The cheeriness was still there, but he heard the underlying sharpness that told of a chip on her shoulder. Dig rocked back onto his heels and looked up again with genuine curiosity then shrugged in acceptance. Even standing, she wasn’t much taller than his kneeling form, but all the same, she crouched and leaned in further to get a good look at the control panel.

“You’re actually right. I usually build computers so elevators are a little bit of a different species, but, hey, wires are wires, right?”

All while muttering under her breath, she pointed out a few connections and had him rejigger the system in much fewer steps than the elevator company’s technicians gave him over the phone. He wouldn’t really know until he tested the elevator out, but her recommendations seemed solid.

Dusting himself off, he gave her a sincere thanks, surprised when she stuck out a hand.

“Felicity Smoak,” Dig raised an eyebrow at the shock of meeting the up and coming CEO and how unfazed she was to shake his grease-stained hand, “Nice to meet you.”

“John Diggle, building engineer,” he returned, “My friends call me Dig.”

With a pleased grin, Felicity started, “Well, Dig, if you ever need help with these beasts again, I’m your girl. Not your girl _girl_. I’m not making a pass at you. I just mean, happy to provide tech support.”

He suppressed a chuckle at her easy flustering, an interesting contrast to her take charge attitude from a few minutes ago.  
Felicity collected her purse and laptop bag from where she left them leaning against the doors and bid him a good night. Only then did Dig remember that it was practically midnight, the best time to repair elevators since no one—or _nearly_ no one—was left in the offices. He’d have to keep an eye out for Ms. Smoak, make sure she didn’t burn out before sharing her special brand of guileless genius with the world.

 

* * *

 

And where one serendipitous meeting with a CEO happened, apparently another was sure to follow.

The next week, Dig was all prepared to step off the elevator once the doors opened, and he would have. Except for the person who crashed straight into him. The lukewarm coffee that ended up crushed between them immediately seeped into his clothes, and Dig was thankful he was wearing a pair of coveralls instead of a suit.

“Are you kidding me?” He looked up from inspecting himself to find a suited man, of course, looking belligerent. “Watch where you’re going! What idiot hired you?”

Before Dig could respond with a snarky, “Your father,” the suit, in all his petulant, over-pampered glory, was whisked away by the elevator. He rolled his eyes at the unpleasant interaction because who doesn’t check to see if an elevator is occupied before walking straight into it then blames the departing passenger for the collision?

Oliver Queen, that’s who.

A day later, he walked in for his morning shift to find the entitled dick in a heated conversation with the security desk.

“For the last time, I don’t know who you’re talking about, hoss.”

Either Rene really had no idea who Oliver was looking for, or he was playing dumb to mess with the guy.

“Oh come on. The guy’s like six-four and built like a refrigerator. He was wearing a mechanic’s uniform or something. How many people wander around this building dressed like that?”

Oh, so _he_ was the target of this fishing expedition. Dig rolled his shoulders back and prepared himself to be fired for some minor, imaginary offense. It was more of an annoyance than anything.

What Mr. Queen probably didn’t realize was that Dig’s usual occupation was president of the property management group that owned the building known as QC headquarters. What most of Starling City probably didn’t realize was that QC was just the largest tenant of the building, hence the naming rights, and not the actual owner (anymore at least). And so if Mr. Queen wanted to fire Dig, when he was filling in as building engineer while they retrofitted the building systems, Mr. Queen was shit out of luck.

Rene rolled his eyes. “In case you haven’t noticed, there are fifty floors in this building. I don’t know every schmuck who walks through the front doors. Is there anything else I can help you with, sir?” The sarcasm was easily detectable, causing Dig to shake his head at Rene’s irreverence.

Oliver also shook his head but probably with a disgusted look on his face and turned around. Dig just quirked an eyebrow at the surprised CEO before Rene rang out with a cheery for him, “Morning, Dig.”

Yeah, Rene was totally fucking with him for kicks.

“Dig, is it?” Oliver asked, justifiably ignoring the clown behind him.

He frowned and left the outstretched hand hanging. “My friends call me Dig. You can call me Mr. Diggle. _Mr. Queen_ ,” he tacked on as an afterthought.

Dig swiped his badge across the sensor and walked through the gates, Oliver following quickly behind. He didn’t bother to slow down. If he’s about to be “fired,” he might as well head to his office.

Surprisingly, Oliver kept pace and stopped him just outside the personnel door. “Look, I wanted to apologize for yesterday. I was in a hurry and I should have been looking where I was going. It was my fault.”

The terse sincerity stopped Dig in his tracks.

Obviously, and for obvious reasons, Oliver Queen was not used to issuing apologies. Still, the man was trying. Dig was positive anyone else in his position, with a sudden attack of conscience after the fact, would have just forgotten the incident and promise themselves to do better the next time. It took a certain amount of character to track down someone who could have been a janitor—not that occupation mattered but _society_ —to apologize. Not many others would have made the effort.

Turning, Dig offered his hand. “Apology accepted. Call me Dig.”

 

* * *

 

Surprisingly, the CEOs kept up the friendly overtures. Oliver always had a nod and salutation for him before they stereotypically bonded over the Rockets’ season, while Felicity kept him busy with suggestions to improve the building systems. Slowly but surely, he became something of a confidante to both of them.

That’s why Dig wasn’t surprised as they both went through assistants like tissues. Calling Oliver difficult to manage was the understatement of the year, and Felicity needed someone with a specific set of qualifications to keep her mind on track. Somehow, neither were satisfied with the clones picked out by their HR departments or sent over from temp agencies.

Felicity, at least, seemed to realize that jamming a square peg into a round hole wasn’t ever going to work because she went out and found herself an octagon instead. Dig had his doubts when she mentioned her plan to him, not the least because she decided to venture into the Glades by herself, yet somehow it worked.

Roy Harper might have been rough around the edges but the kid had street smarts for days. Dig could tell because the first thing Roy did was befriend the building staff, himself included, and the delivery people. When most office workers treated them like a piece of gum stuck to their shoe, mere civility earned the polite drones the royal treatment. Roy did them one better by occasionally springing for a tray of coffees from that fancy place Felicity liked.

And say what you will about the Queen family, but manners had been bred into their pedigree (Oliver apparently being the exception). Not long after Thea took up the unenviable position of Oliver’s assistant, she went around to introduce herself to the staff and thank them for making everyone’s lives a little easier and more seamless. And, hey, if they all got Starbucks gift cards on the last day of each month, everyone had a sneaking suspicion about who it came from.

So when Dig happened to be in the security office early one morning and saw Roy sprinting for an elevator on the monitors, he may have kept his finger on the open button, just for a second. He meant to finish his shift and leave after that, but even without sound, the sparks flying off the two young assistants had been almost palpable. That’s when he started amusing himself by keeping an eye on the overworked characters in his building and their slow-blossoming romance.

They were two sides of the same coin. Thea was sincere in wanting to express her appreciation for others around her but she didn’t know how to accomplish that without her money. Roy’s thoughtfulness was equally as genuine, but his instinct was to rely on ill-gotten gains with monetary resources as a last resort.

That difference was obvious when they showed up at his office with a proposition and a half-baked idea to trap their bosses in an elevator like this was an actual rom-com. Roy turned up with their special handshake and a fern—according to Felicity, they thrived in low light AKA his windowless pit—and Thea with a good, old-fashioned bribe. Dig stifled his laughter as he accepted both offerings.

Despite the disastrous first meeting—Dig was sure Felicity hadn’t recognized his voice only because of her sheer panic, and Oliver seemed to be on a hot streak when it came to pissing off people in elevators—Thea and Roy were undeterred. Suddenly, he had another couple to add to his daytime viewing. The pair of assistants were relentless in their matchmaking, and Dig had no idea how Felicity and Oliver didn’t catch on.

 

* * *

 

After over two months of watching what he deemed circumstantial evidence, Dig’s finally cooking with gas.

_Coincidentally_ , not too long after Roy and Thea started their matchmaking scheme, Oliver and Felicity began arriving to the office at approximately the same time. The assistants never picked up on it, because they were either already at their work stations or not there yet and oblivious to when the bosses rolled in, but it was certainly a _coincidence_.

(That they left their offices at the same time wasn’t nearly as remarkable since they were always, by _sheer_ happenstance, scheduled for the same events.)

“Oh hello,” he mutters when Oliver’s elevator stops at Felicity’s floor. The movement happened to catch his attention since it was past eleven at night, and there was absolutely no other movement on the monitors. All sane people had abandoned ship for the night.

Felicity steps onto the elevator, presumably greeting Oliver with an actual smile on her face. Dig is shocked, absolutely shocked he repeats with an eye roll, when the pair drift closer, their body language screaming flirtation. Oh so the prize idiots have finally worked out that they’re both single, attractive, and the epitome of propinquity.

His sarcastic commentary vanishes when Oliver’s hands land on Felicity’s waist at the same time she throws her arms around his neck. Slumping into his worn office chair, Dig sits in stunned silence as they make out the entire way down to the lobby. By the time the doors slide open, they’re more or less presentable and the entire elevator apart.

Then he breaks down in hysterical laughter.

 

* * *

 

“What the—” Roy complains when Dig grabs him by the arm and unceremoniously drags him into his closet of an office. “Dig! I’m going to be la—”

His protests immediately die down when Roy catches sight of Thea already in the office. She’s seated in his ancient desk chair and shamelessly taking advantage of the privacy to spin around in fast circles.

“Hi,” Roy offers with a moonstruck look that Thea returns.

Dig just rolls his eyes. These two are worse than their bosses, now that he’s had a chance to observe both couples. Hell, he might have to engineer another “trapped in the elevator” situation if they don’t get their shit together soon.

“What are we doing here, Mr. Diggle?” Thea asks, suddenly the image of propriety and manners again.

“Dig, I told you,” he reminds her absently. After nudging her out of the chair, he’s pulled up the security footage he saved from last week. Roy and Thea are quiet behind him, probably exchanging lovesick glances, as he fast forwards through the tape.

“Son of a bitch!”

Surprisingly, the exclamation comes from Thea while Roy just rolls his eyes.

“Do _not_ say “I told you so.” Of course, we had to interfere, and you got on board pretty damn quickly.” The pixie-sized woman threatens her male counterpart, who wisely mimes zipping his mouth shut. “I’m going to give him so much shit for this.”

Roy nods in agreement before bravely muttering, “You shouldn’t call your mother a bitch.”

The boy rushes for the door at the same time Thea turns her stink eye on him. With an amused head shake, Dig watches them chase each other out, hoping he’ll somehow obtain an update on the two couples without having to ask.

 

* * *

 

He’s double-checking the punch list work for a new tenant on Felicity’s floor, so it’s not that surprising when he runs into the woman herself. What is surprising is that the woman herself runs headlong into his chest. Felicity throws her phone up in surprise, and only his quick hands save the device from an untimely end on the fancy tile.

“Thanks, Dig,” she breathes in gratitude.

“No problem, Felicity. Where are you off to in such a hurry?”

Her coat is half-on, hanging from one shoulder, while her hastily stuffed purse is wide open. She flushes a little at her relatively unkempt appearance. Seriously, he’s seen this woman at midnight after a full day of meetings and lab work with her makeup still perfectly in tact. But it’s barely six at night, and probably no one remembers the last time Felicity left her office before dinner without serious intervention.

“Oh, nowhere in particular,” she badly and baldly lies. “Roy’s been cutting back on my social engagements, and I hadn’t realized how much I was used to getting out of here at night.”

He hums skeptically. So that’s how Thea and Roy are getting their revenge. Instead of creating more opportunities for Felicity and Oliver to run into each other, they’re drying up the well and making them scramble to find time together. It’s kind of genius in its simplicity.

With an amused smile, he follows her into the elevator, waving goodbye as she rushes out the revolving doors instead of heading for the garage. After a few minutes of loitering in the lobby, shooting the breeze with Rene, Dig’s there waiting when a flustered Oliver steps off the elevator. The man is so frantic to leave, he barely acknowledges Dig as he takes off in a near sprint, following Felicity’s tracks.

“They’re totally banging, aren’t they, hoss?” Rene asks with a raised eyebrow.

Dig just shakes his head, barely suppressing his grin. “Do your job.”

Their attention is drawn outside by a sudden burst of honking. In the dim twilight, he can just make out Oliver’s silhouette darting across multiple lanes of traffic, apparently too impatient to wait for a walk signal. Rene bursts out with a laugh, and Dig can’t hide his amusement this time.

Those two meddling assistants are _evil_ geniuses.

 

* * *

 

Dig’s even less surprised when he emerges from the staff hallway into the lobby early, _early_ one morning and finds a showdown of sorts happening in front of the elevators. Clearly, Roy and Thea have finished toying with their supposedly oblivious bosses and have decided to force the issue this morning. Dave from the night shift is doing his best to pretend like he’s not eavesdropping on whatever the hell is going on, but the man wasn’t hired for his subtlety.

Can’t exactly blame Dave, though, when Thea’s yelling things like, “If you wanted to be a secret couple, maybe stop making out in elevators!”

True to description, Felicity’s usually impeccable lipstick is smudged, and Oliver’s tie is all... wrangled.

“What’s going on here?” he greets his favorite unwitting soap opera as if it weren’t completely obvious.

The tension doesn’t quite break, but Felicity drops her crossed arms at the same time she releases a deep sigh. Oliver’s hand twitches by his side, and he guesses the man is restraining himself from offering Felicity a comforting touch.

“Apparently, we’re just pawns for their amusement.” Both Roy’s and Thea’s defensive expressions drop at her disappointed tone. Dig can’t even hide his wince of sympathy. “And after all I’ve done for you, Roy Harper!”

It’s the dramatic overselling that does it. Roy loses the hangdog look and rolls his eyes heavily, while Thea waffles between looking annoyed and repentant. That’s right. Thea still technically doesn’t even know Felicity despite how well she must know Felicity through Roy by now.

“You’ve got to be kidding me!” Roy complains, squinting at his boss accusingly. “You’ve known this _entire_ time, haven’t you? Both of you?”

Felicity rolls her eyes just as hard. “I _am_ a genius, Roy. Even then, it doesn’t take one to figure out what you two have been up to this whole time.”

“Yeah, ‘cause Ollie’s definitely _not_ ,” Thea kicks in unthinkingly. Unthinkingly because now her brother’s leveling her with an offended glare that she squirms under. “Sorry,” she mutters without an ounce of regret.

The couples re-engage in their staring contest until Dig clears his throat loudly, reminding them that they’re in a public lobby that will eventually be full of people trying to get to work.

“So now what?” Roy asks reluctantly. He’s kind of huddled in on himself as if bracing for a natural disaster.

Belatedly, Dig realizes that he’s preparing to get fired or worse for daring to meddle in Felicity’s private life. Which would be the appropriate reaction for anyone but Felicity, who went out of her way to track down and hire her pickpocket. In fact, the soft-hearted woman sighs at Roy’s physical reaction and folds almost instantly.

“We go upstairs and go to work,” she firmly reassures him that his job isn’t in jeopardy. “Then we’re all leaving at a reasonable hour tonight, no later than six.”

Felicity shyly smiles up at Oliver, who returns the gesture immediately. “Because we have date night, _and_ so do you two.”

Roy splutters while Thea bites down on her lip to suppress a smile.  
“I don’t need my brother’s _girlfriend_ setting me up on a date,” the young Queen snottily replies. Good thing they can all hear the teasing in her tone.

Oliver arches an eyebrow at the sass. “And I didn’t need my annoying little sister setting me up, but here we are. Do you not want to go?” he asks carefully, offering her an out that he looks all too willing to enforce. In fact, Felicity nudges him, offended on Roy’s behalf.

“No, no!” Thea immediately responds before frowning, “I mean, yes. Or, I _do_ want to go, whichever way that works. That is, if you want to?” she, suddenly bashful, directs to Roy the statue.

The young man doesn’t respond verbally, for once not having the smooth demeanor Felicity hired him for. Instead, he just nods enthusiastically, causing Felicity to hide an affectionate chuckle behind her hand.

“Great,” Oliver grimaces, somehow not sounding like the most thrilled big brother to have helped matchmake his little sister. “Upstairs!” He drops a hand on Thea’s shoulder to frog-march her to the open and waiting elevator while Felicity and Roy trail behind them.

Dig lingers for a few moments after the doors close because they quickly spring back open. “Out of order,” he deadpans, holding up the sign he came out to place as they sheepishly spill back out.

After waving off Felicity’s offer to help, he overhears Oliver hissing to her, “I _knew_ I hit the button. Told you it wasn’t my fault.”

_Nope_ , Dig smirks to himself. Wasn’t _only_ Oliver’s fault he was getting tired of watching them play the world’s weirdest mashup of tag and hide and go seek where Oliver and Felicity tried to hide their relationship from Roy and Thea who were trying to keep them apart as revenge and simultaneously catch them in the act. When the assistants showed up just as the bosses were about to undertake their daily, if not twice daily, elevator make out session, Dig couldn’t pass up the opportunity to manufacture some early morning entertainment. All it took was the press of one little button.

After all, he does love love in enclosed spaces.

 


End file.
